Tabernaelegantine B






Names

    • Tabernaelegantine B

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@H]2C[C@@]3(C(OC)=O)C1[N@](CCC4=C3NC5=C4C=CC(OC)=C5[C@H]6C[C@H]7[C@H](CC)CN(C)[C@H](CC8=C6NC9=CC=CC=C89)[C@@H]7C(OC)=O)C2

  • InChI

    InChI=1S/C43H54N4O5/c1-7-24-17-23-20-43(42(49)52-6)39-28(15-16-47(21-23)40(24)43)27-13-14-34(50-4)36(38(27)45-39)31-18-29-25(8-2)22-46(3)33(35(29)41(48)51-5)19-30-26-11-9-10-12-32(26)44-37(30)31/h9-14,23-25,29,31,33,35,40,44-45H,7-8,15-22H2,1-6H3/t23-,24-,25+,29-,31+,33+,35+,40?,43-/m0/s1

  • Molecule Class: Alkaloids
  • TPSA: 99.89000000000001
  • #RotBonds: 6
  • MW: 706.9280000000002
  • HBD: 2
  • HBA: 7
  • logP: 6.568800000000007
  • Chemical Formula: C43H54N4O5


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. bufalina China 403123 Cai20170220
    T. corymbosa Malaysia, China 1679252 GK604

External Databases


References

  • Bisindole alkaloids from Tabernaemontana corymbosa. Phytochemistry, 2018 (PMID 29758521).
  • Cytotoxic Monoterpenoid Indole Alkaloids from Tabernaemontana corymbosa as Potent Autophagy Inhibitors by the Attenuation of Lysosomal Acidification. J Nat Prod, 2020 (PMID 32356659).
  • Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina. Planta Med, 2018 (PMID 29689587).

Compound-Protein Relationships


Compound Activities

    • Cytotoxicity
    • Antiinflammatory
    • Acetylcholinesterase inhibitory
    • Lysosomal acidification

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -5.71
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney 18.05
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability 3098.72
    Distribution Blood-Brain Barrier (Central Nervous System) -2.82
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.26
    Plasma Protein Binding 88.66
    Steady State Volume of Distribution 5.16
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Inhibitor
    Excretion Clearance 12.47
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -75.26
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.41
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.64
    Micronucleos Toxic
    NR-AhR Safe
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -5623550.01
    Rat (Acute) 2.96
    Rat (Chronic Oral) 2.4
    Fathead Minnow 7101.46
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 629175.34
    Hydration Free Energy -2.92
    Log(D) at pH=7.4 6.04
    Log(P) 6.2
    Log S -5.57
    Log(Vapor Pressure) -20648.48
    Melting Point 294.43
    pKa Acid -111.94
    pKa Basic 6.3